Chicago Jazzfest-Day 1
Labor Day weekend has arrived, which means that winter is fast approaching. But before we bring out the heavy coats and sidewalk salt, we have one last opportunity to enjoy the summer: Chicago Jazzfest, which opened today with a series of performances at the Chicago Cultural Center before moving across the street to Millennium Park. The festival commandeers two performance spaces in the Cultural Center, The Preston Bradley Hall and the Claudia Cassidy Theater. During the afternoon performances, I ping-pong back and forth between the two spaces. The Shy Shěks opened the Cassidy Theater’s afternoon lineup, with the Extraordinary Popular Delusions kicking the festivities off in the Preston Bradley Hall.
The two groups are polar opposites. The Shěks draw from the likes of Django Reinhardt and Maurice Chevalier, among others from way back in the day. The band is led by rhythm guitarist Nick Rutz, with his sister, Cassondra Porayko serving up the vocals. Finishing the mix are Ethan Adelsman on violin and John Garza on guitar. Lets face it, any group that brings violinist Stéphane Grappelli to mind is alright. I must admit, as a singer Porayko is not to my taste. Her gestures and facial expressions were great, but I found her voice to be a bit thin. As for the numbers, the group took on Ethel Water’s Moon Glow, Rudy Vallee’s theme song, My Time Is Your Time, and Sweet Sue, a classic dating to 1928
As I approached the Claudia Cassidy Theater, I knew exactly what I was about to hear. Saxophonist Edward Wilkerson, Jr. was leading an exercise in somewhat free jazz, with Jim Baker playing both piano and violin, Brain Sandstrom on guitar, Christopher Dammann on bass, and Steve Hunt on drums. In my younger days, I would have loved the cacophony of sounds. As I age, less so. Nevertheless, the musicians hued the line, meaning that there was some linearity in what they were playing. It is hard not to like whatever Wilkerson and Baker choose to deliver.
Following Wilkerson and company’s effort, I headed back to the Preston Bradley Hall, where the Tom McCarthy Quartet was paying to tribute guitarist John McLaughlin’s 1969 album, Extrapolation, which I recall discovering after first encountering McLaughlin’s Inner Mounting Flame excursion into jazz fusion. I remember Extrapolation being a little more acoustic than what I heard this afternoon, but McCarthy did live up to the expectations created by any reference to McLaughlin.
I left McCarthy looking forward to what was coming next. Saxophonist Ernest Dawkins was back once again, with the Young Masters, an ever changing group of student musicians who Dawkins mentors. Back this year were bassist Galen Morris and drummer Mac Ramsey. Dawkins also brought along a vibist, a second bassist, and a guitarist. The music was straight-ahead, no-nonsense jazz, with Dawkins giving his young proteges (don’t call them kids if you want to stay on Dawkins’ good side) ample opportunity to shine. According to Dawkins, all of the compositions were written by the students.
Later in the afternoon, Tatsu Aoki’s Toyoaki Ensemble performed on the Preston Bradley stage, offering up a Japanese take on jazz. While alto saxophonist Mai Sugimoto brings recognizable jazz lines to the mix, I am not convinced that what the ensemble produces should be characterized as jazz, even under an expansive definition of the term. That, however, is not meant as a criticism. Playing the shamisen ( a lute-like instrument), Aoki always produces intriguing sounds. I always love Koichi Hiraishi’s work on the taiko drums. Her athletic strokes produce highly satisfying visuals.
During the course of the afternoon, the audience was also treated to performances by pianists Julius Tucker’s quartet and guitarist’s Larry Brown, Jr.’s quartet. Both groups offered up some straight-ahead, no-nonsense jazz. Along the way, composer and pianist Robert Glasper sat for an interview with pianist Robert Irving that addressed Glasper’s work scoring movies.
At 5:00 PM, I headed over to the Pritzker Pavilion for the evening performances. It certainly was a beautiful afternoon-still hot, but the heat was more tolerable, probably because of my proximity to Lake Michigan. The Brown sisters (Maggie and Africa) opened the evening performances, with a three-song set. I am not a Maggie Brown fan, so I was not troubled by the short set. For my money, the sisters dwelled too long on their legendary father, Oscar Brown, Jr. They even played multiple interview clips with him speaking about music, which meant they turned in a largely anodyne set.
Vibist Joel Ross followed the Browns. Now living in Brooklyn, Ross’ return to Chicago was a welcome one. Much credit goes to Ross for his generosity. At times I would have thought I was listening a group led by Ross’ saxophonist Devin Daniels. While I can’t complain about the quality of the group’s musical effort, Ross needs to learn how to structure a set. By my count, he played three or four long numbers, which blended together because they all shared the same tempo and orchestration. By the end of the set, I was bored despite the promising beginnings.
At 7:45 PM, the headliners took the stage. Going in cold, I had low expectations. Bill Charlap is the premier pianist these days, but he leaves me cold. Nondescript is the word that comes to mind. Not bluesy, not soulful, not free, not hard driving, not trad. Dull.
Turns out that Bridgewater brings out a different Charlap. An odd couple if there ever was one. Remember the Carol Burnett Show? Well, think of Bridgewater as Tim Conway and Charlap as Harvey Korman. Conway always successfully disrupted Korman’s effort to play it straight. Bridgewater managed to bring a smile to the otherwise reserved Charlap’s face. She broke him. The attractive woman takes on the staid banker.
Tonight, the duo looked to the American songbook for guidance, opting for selections associated with Duke Ellington. Among the selections were Cole Porter’s Love for Sale, The Man I Love, Beginning to See the Light, Caravan, Honey Suckle Rose, and Lost Without You.
Probably the evening’s most touching moment came when Bridgewater recounted the phone call she had yesterday with Diana Reeves. It was Reeves who informed Bridgewater that Cassandra Wilson had died. Bridgewater’s tears were visible as she painfully recounted the conversation.
But Bridgewater carried on, singing Billie Holiday’s Fine and Mellow—”Love is like a faucet; it turns on and off.” Along the way, she imitated a trumpet, fell into a baby-girl voice, and whistled. Needless to say, I was pleasantly surprised by pairing.
Overall, an enjoyable first day of music. Unfortunately, the music was enjoyed by too far few people. Two-thirds of the great lawn was surprisingly empty. Was it the week of intense heat that kept people away? I don’t know, but hopefully the attendance will be much larger tomorrow.
Click on an Image to Enlarge It. The Images Are Not Necessarily in Exact Chronological Order]
Brian Sandstrom Exchanging His Guitar for a Flute
Edward Wilkerson Jr. Is Anything But Deluded
Jim Baker Exchanging the Piano for a Violin
Bassist Christopher Dammann Mesmerized By Extraordinary Delusions
Returning to His Guitar
Jim Baker Working the Keys
John Garza, Another Shy Shẽk, Playing a Colorful Hollow-Body Guitar
Nick Ruiz Is One of the Shy Shēks
Ethan Adelsman Isn't Shy When Using His Bow
Cassondra Porayko Gesturing as She Belts Out a Number
Lulled by the Melody
Galen Morris Returning as a Young Master
Mac Ramsey Playing the Drums
Ernest Dawkins Leading the Young Masters
A Young Master Playing the Vibes
A Young Master Playing Trumpet Under the Tutledge of Ernest Dawkins
Double the Fun
Larry Brown Jr. Leading His Quartet
Julius Tucker Looking Pleased
Kyle Swan Laying Down the Beat for Julius Tucker
Christan Diillingham Adding Buttom
Julius Tucker Leading His Quartet
Mai Sugimoto Adding Alto Sax to the Toyoaki Ensemble
Kioto Aoki Playing a Hand Drum
Tatsu Aoki Playing the Shamisen
Koichi Hiraishi Plucking His Bass as Part of the Toyoaki Ensemble
Leading the Toyoaki Ensemble
Coming Down Hard
Bassist Micah Collier Playing an Introductory Number Before Robert Glasper is Interviewed by Robert Irving III
Playing with Micah Collier
Robert Glasper Surveying the Audience Before His Session
Robert Irving III Interviewing Robert Glasper
Trumpter Dakarai Barclay Playing with the Julius Tucker Quartet
A Plug for the Jazz Institute of Chicago
Singing 'Life Every Voice and Sing' Before the Festivities Begin
Playing the National Anthem
Today’s Lineup
Maggie and Africa Brown Putting Words to Charlie Parker's Ornithology
Almarie Wagner (L) Standing With Her Good Friend, Judith Stein (aka That Crazy Jazz Lady)
Pianist Tyler Bullock II Accompaning Joel Ross
Alto Saxophonist Devin Daniels Playing With Vibist Joel Ross
Two Hard Core Jazz Afficiandos Who Lost Their Heads Over a Tenor Sax Solo
Jeremy Dutton Adding His Own Good Vibes to the Mix
Joel Ross Casting Good Vibes
Alone Together (Bill Charlap and Dee Dee Bridgewater)
Seated
Perfection
Bill Charlap Had Better Watch His Back
Dee Dee Bridgewater Having a Good Laugh With Bill Charlap
Dee Dee Leaning Back
Together Again
Teeth
Singing a Lament
Soaking Up the Applause
Copyright 2026, Jack B. Siegel, All Rights Reserved. Do Not Alter, Copy, Display, Distribute, Download, Duplicate, or Reproduce Without the Prior Written Consent of the Copyright Holder.



